Anthracene dye and process of making same.



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homologue, or a derivative thereof, by'heat. mg such compound either alone or in the presence of a condensing agent, audit is stated in'the said specification that the said coloring matters dye cotton, from the vat, yielding orange shades. I

v I have now discovered that by treating the aforesaid coloring matters with a halogenagent, such for instance as halogen itself, or a substance evolving halo en, new coloring matters can be obtained which dye cotton, from the vat, redder shades than those obtained from the original coloring matters. The new coloring matters themselves, inv the condition of powder possess, generally, properties similar to those of the so coloring inatters'from which they are produced, their shades, however, are different. They consist of from yellow to brown powders which are insoluble in water and in dilute acids and in dilute alkalies and are 35. soluble in concentrated sulfuric acid and in hot nitrobenzene and in hot anilin and which are also soluble in alkaline hydrosulfitevyielding cherry red vats which produce on cotton blue-red shades which shades on washing 40 are converted into bright orange-red.

The following examples will serve to illustrate further the nature of my invention and eiplain how it can be carried into practical e set, but my invention is not confined to theseexampies. The parts are by weight. Example 1. W'ell mix ten (10) parts of the product obtainable by heating 2.2 -dimethyi-Ii.1dianthraquinonyl with 'alcolioiic potash as described in Example 1 of the to aforesaid specification with one hundred "(100) parts of nitroloenzene and, while at ordinary tem erature, addseven ."(7). parts of sulfuryl c orid (80 GB). Stir for three (3) hours at a temperature of from sixty Specification of Letters Patent. Application flied Novenbar 21. 1906 Serial No. 844.4;88s

ic, residing at Mannheim,

Patents-ti to seyenty ('20), degreesoeutigrade 535 and, when cold, addoae hundred (ice parts" of alcohol. ene as wash with aloe-- he! and then with water. ,fiie chlorinated nroduet can be recrystallised from fitro 'enzene and obtained in form of lam so red'nleefdles which areinsoiulale in water and "'ee and-are soluloiein concentrated, F sulfuric. acid, yielding a deep. solution, and in clean; citwentythree (23) cent. a dull blue solution. They are difficnltly selubie in glacial acetic acid yielding "a silent solutiesn; i V xamrile 2;. Well min ten (10) parts of the coloring matter obtainable by heating 2.2- dimethyl-I.1-dianthraquinonyl with alco 7o holic potash as described in Example i of the aforesaid specification, with one hundred (100) parts of nitrobenzene and, while stir ring at ordinary'temperaturapass a current of chlorin slowly into the mixture for from thirty (30),, to forty-five (45), minutes. The brown-yellow color of the liquid turns to orange-red. Dilute with one hundred (100) parts of alcohol," filter and wash with arcohol and, if necessaryfwit'n Water,

Now what I claim is: I 1. The process for the roduction of anthracene coloring matter oy heating a 2.2 dimethyl-l.i-dianthraquinonyl body and treating the resulting compound with a halogenizing agent.

2. The process for the production of anthracene coloring matter hy heatin a 2.2- dimethyl l.1-dianthr1iquinonyl be 1 with a condensing a cut and treating theresulting es compound wit a halo enizing agent.

3. The process for t e production of an thracene coloring matter by heating 2.2 dimethyl-l.1dianthraquinonyl body with alcoholic ctash and treating the resulting es compolm. with a halo cnizing agent.

4. The process for t is production of anthraoene coloring matter by heating 2.2- dimethyl-i 1 -diantliraquinony1 with also holic Ifotash. and treating the resulting corn we poun with a halo enlzmg agent.

' 5. The process ior the production. of an thracene coloring matter by heating 232' dimethyl-i.l dianthraquinonyl body and treating the resulting compound with sul ce 'furyl chlorid;

6. The process, for the production of an thraeenc coloring matter by heating; a 2.2-

dimethyll.1-dianthraquinonyl body with a condensing agent and treatingi the resulting compound withsulfuryl chlori 7. The process for the reduction of anthracene coloring matter y heatin a 2.2 dimethyl-l.1-dianthraquinonyl b0 y with 'alcoholic (fotash and treating the resulting compoun with sulfuryl chlorid 8; The process for the reduction of anthracenecoloring matter y heating a 2.2- dime thyl1 1 -dianthraquinonyl with alco 'holic rPotash and treating the resulting compoun with sulfuryl chlorid. 9; As new articles of manufacture the new anthracene coloring matters which can. be obtained b treatlng with a halogenizing agent a co oring matter which can be ob: tained as aforesaid from a 2.2-dimethyl-1.1-

-dianthraquinonyl body, which new coloring cherry red vats -whichsproduce on cotton blue-red shades which shades on washing are converted into bright orange-red.

' 10. As a new article of manufacture the new anthracene coloring matter which can be obtained by treating with sulfuryl chlorid the coloring matter which can be obtained by heatin 2.2-dimethyl-1.1-dianthraquinonyl with 5100110110, potash, which new coloring matter is a brown powder insolublein Waterand in dilute acids and in dilute alkalies and soluble in concentrated sulfuric acid and in hot nitrobenzenc and in hot anilin and is also soluble in alkaline hydrosulfite yielding a cherry red vat which produces on cotton blue-red shades which shades on washing are converted into bright orange-red.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses. g MAX ALBERT KUNZ.

Witnesses: H. W. HARRIS,

' 'ERNEST F. EHRHARDT. 

